The benzaldehyde oxidation paradox explained by the interception of peroxy radical by benzyl alcohol

Nature Communications

Volumn 5, Issue , 2014, Pages

  Sankar, Meenakshisundaram ^a   Nowicka, Ewa ^a   Carter, Emma ^a   Murphy, Damien M ^a   Knight, David W ^a   Bethell, Donald ^b   Hutchings, Graham J ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BENZALDEHYDE; BENZOIC ACID; BENZYL ALCOHOL; HYDROGEN; PEROXY RADICAL;

AIR TEMPERATURE; ALCOHOL; ALDEHYDE; CATALYST; OXIDATION; PEROXY RADICAL;

AIR; ARTICLE; AUTOOXIDATION; CATALYST; ELECTRON SPIN RESONANCE; OXIDATION; ROOM TEMPERATURE; SPIN TRAPPING;

EID: 84896890531     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms4332     Document Type: Article

References (43)

1. Sheldon, R. A. & van Bekkum, H. Fine Chemicals Through Heterogeneous Catalysis (John Wiley & Sons Inc., 2001).
2. Sheldon, R. A. & Kochi, J. K. Metal-Catalysed Oxidations of Organic Compounds (Academic Press, 1981).
3. Hudlicky, M. Oxidation in Organic Chemistry (American Chemical Society, 1990).
4. Backvall, J.-E. Modern Oxidation Methods2nd edn (Wiley-VCH Verlag, 2010).
5. Miyamura, H., Matsubara, R., Miyazaki, Y. & Kobayashi, S. Aerobic oxidation of alcohols at room temperature and atmospheric conditions catalyzed by reusable gold nanoclusters stabilized by the benzene rings of polystyrene derivatives. Angew. Chem. Int. Ed. Engl. 46, 4151-4154 (2007). (Pubitemid 46959939)
6. Enache, D. I. et al. Solvent-free oxidation of primary alcohols to aldehydes using Au-Pd/TiO2 catalyst. Science 311, 362-365 (2006). (Pubitemid 43132657)
7. Abad, A., Concepcion, P., Corma, A. & Garcia, H. A collaborative effect between gold and a support induces the selective oxidation of alcohols. Angew. Chem. Int. Ed. Engl. 44, 4066-4069 (2005). (Pubitemid 40886449)
8. Johnston, E. V. et al. Highly dispersed palladium nanoparticles on mesocellular foam: an efficient and recyclable heterogeneous catalyst for alcohol oxidation. Chem. Eur. J. 18, 12202-12206 (2012).
9. Yamaguchi, K. & Mizuno, N. Supported ruthenium catalyst for the heterogeneous oxidation of alcohols with molecular oxygen. Angew. Chem. Int. Ed. Engl. 41, 4538-4542 (2002). (Pubitemid 35462410)
10. Karimi, B., Biglari, A., Clark, J. H. & Budarin, V. Green, transition-metal-free aerobic oxidation of alcohols using a highly durable supported organocatalyst. Angew. Chem. Int. Ed. Engl. 46, 7210-7213 (2007). (Pubitemid 47517910)
11. Su, F. Z. et al. Ga-Al mixed-oxide-supported gold nanoparticles with enhanced activity for aerobic alcohol oxidation. Angew. Chem. Int. Ed. Engl. 47, 334-337 (2008).
12. Mori, K., Hara, T., Mizugaki, T., Ebitani, K. & Kaneda, K. Hydroxyapatitesupported palladium nanoclusters: a highly active heterogeneous catalyst for selective oxidation of alcohols by use of molecular oxygen. J. Am. Chem. Soc. 126, 10657-10666 (2004). (Pubitemid 39129166)
13. Mallat, T. & Baiker, A. Oxidation of alcohols with molecular oxygen on solid catalysts. Chem. Rev. 104, 3037-3058 (2004).
14. Sheldon, R. A., Arends, I. W. C. E., ten Brink, G.-J. & Dijksman, A. Green, catalytic oxidations of alcohols. Acc. Chem. Res. 35, 774-781 (2002).
15. Li, G. et al. Solvent-free oxidation of benzyl alcohol with oxygen using zeolite-supported Au and Au-Pd catalysts. Catal. Lett. 110, 7-13 (2006). (Pubitemid 44214682)
16. Enache, D. I. et al. Solvent-free oxidation of benzyl alcohol using titania-supported gold-palladium catalysts: effect of Au-Pd ratio on catalytic performance. Catal. Today 122, 407-411 (2007). (Pubitemid 46702499)
17. Meenakshisundaram, S. et al. Oxidation of alcohols using supported gold and gold-palladium nanoparticles. Faraday Discuss. 145, 341-356 (2010).
18. Cao, E. et al. Reaction and Raman spectroscopic studies of alcohol oxidation on gold-palladium catalysts in microstructured reactors. Chem. Eng. J. 167, 734-743 (2011).
19. Mantle, M. D. et al. Pulsed-field gradient NMR spectroscopic studies of alcohols in supported gold catalysts. J. Phys. Chem. C 115, 1073-1079 (2010).
20. Conte, M., Miyamura, H., Kobayashi, S. & Chechik, V. Enhanced acyl radical formation in the Au nanoparticle-catalysed aldehyde oxidation. Chem. Commun. 46, 145-147 (2010).
21. Fristrup, P., Bahn Johansen, L. & Christensen, C. H. Mechanistic investigation of the gold-catalyzed aerobic oxidation of aldehydes: added insight from Hammett studies and isotopic labelling experiments. Chem. Commun. 2750-2752 (2008). (Pubitemid 351832624)
22. Bäckström, H. L. J. The chain-reaction theory of negative catalysis. J. Am. Chem. Soc. 49, 1460-1472 (1927).
23. Jorissen, W. P. & van der Beek, P. A. A. The oxidation of benzaldehyde. Rec. Trav. Chim. Pays-Bas 49, 138-141 (1930).
24. Mulcahy, M. F. R. & Watt, I. C. Mechanisms of oxidation of benzaldehyde. Nature 168, 123-124 (1951).
25. Partenheimer, W. The high yield synthesis of benzaldehydes from benzylic alcohols using homogeneously catalyzed aerobic oxidation in acetic acid. Adv. Synth. Catal. 348, 559-568 (2006). (Pubitemid 43586837)
26. McNesby, J. R. & Heller, C. A. Oxidation of liquid aldehydes by molecular oxygen. Chem. Rev. 54, 325-346 (1954).
27. Partenheimer, W. & Grushin, V. V. Synthesis of 2,5-diformylfuran and furan- 2,5-dicarboxylic acid by catalytic air-oxidation of 5- hydroxymethylfurfural. Unexpectedly selective aerobic oxidation of benzyl alcohol to benzaldehyde with metal/bromide catalysts. Adv. Synth. Catal. 343, 102-111 (2001). (Pubitemid 33673942)
28. Kovtun, G. et al. Oxidation, redox disproportionation and chain termination reactions catalysed by the Pd-561 giant cluster. Adv. Synth. Catal. 344, 957-964 (2002).
29. Sankar, M. et al. Controlling the duality of the mechanism in liquid-phase oxidation of benzyl alcohol catalysed by supported Au-Pd nanoparticles. Chem. Eur. J. 17, 6524-6532 (2011).
30. Bamford, C. H., Tipper, C. F. H. & Compton, R. G. Liquid Phase Oxidation (Elsevier, 1980).
31. Janzen, E. G., Davis, E. R. & DuBose, C. M. Spin trapping chemistry of acyl radicals. Magn. Reson. Chem. 33, S166-S173 (1995). (Pubitemid 126009268)
32. Smith, M. B. & March, J. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 6th edn, 1619 (Wiley-Blackwell, 2007).
33. Klima, J. et al. Spin trapping in electrochemical processes: trapping of radical intermediates in the electrooxidation of substituted 1,4-dihydropyridines. J. Electroanal. Chem. 161, 205-211 (1984).
34. Janzen, E. G., Coulter, G. A., Oehler, U. M. & Bergsma, J. P. Solvent effects on the nitrogen and b-hydrogen hyperfine splitting constants of aminoxyl radicals obtained in spin trapping experiments. Can. J. Chem. 60, 2725-2733 (1982).
35. Swauger, J. E., Dolan, P. M., Zweier, J. L., Kuppusamy, P. & Kensler, T. W. Role of the benzoyloxyl radical in DNA damage mediated by benzoyl peroxide. Chem. Res. Toxicol. 4, 223-228 (1991).
36. Haire, D. L., Oehler, U. M., Krygsman, P. H. & Janzen, E. G. Correlation of radical structure with EPR spin adduct parameters: utility of the proton, carbon-13, and nitrogen-14 hyperfine splitting constants of aminoxyl adducts of PBN-nitronyl-13C for three-parameter scatter plots. J. Org. Chem. 53, 4535-4542 (1988).
37. Buettner, G. R. Spin trapping; ESR parameters of spin adducts. Free Radic. Biol. Med. 3, 259-303 (1987).
38. Howard, J. A. & Tait, J. C. Electron paramagnetic resonance spectra of the tert-butylperoxy and tert-butoxy adducts to phenyl tert-butyl nitrone and 2-methyl-2-nitrosopropane. Oxygen-17 hyperfine coupling constants. Can. J. Chem. 56, 176-178 (1978).
39. Merritt, M. V. & Johnson, R. A. Spin trapping alkylperoxy radicals, and superoxide-alkyl halide reactions. J. Am. Chem. Soc. 99, 3713-3719 (1977).
40. Ohto, N., Niki, E. & Kamiya, Y. Study of autoxidation by spin trapping. Spin trapping of peroxyl radicals by phenyl N-t-butyl nitrone. J. Chem. Soc. Perkin Trans. 2 1770-1774 (1977).
41. Perkins, M. J. in Advances in Physical Organic Chemistry 17 (eds Gold, V. & Bethell, D.) 1-64 (Academic Press, 1981).
42. Janzen, E. G., Evans, C. A. & Nishi, Y. Kinetic study of radical production in the thermal decomposition of benzoyl peroxide by electron spin resonance spin trapping (spin counting). Rate (and substituent effect on the rate) of spin trapping by competitive scavenging of benzoyloxy radicals with galvinoxyl. J. Am. Chem. Soc. 94, 8236-8238 (1972).
43. Kotake, Y., Kuwate, K. & Janzen, E. G. Electron spin resonance spectra of diastereomeric nitroxyls produced by spin trapping hydroxylalkyl radicals. J. Phys. Chem. 83, 3024-3029 (1979).